Triphenylphosphine → HCID 22807221, Verbindung

HRID 614555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614555
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6](C(O)=O)/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC([N+](=NC(OCC)=O)[O-])=O)C>O1CCCC1.CCOCC.CCCCC>[O:5]=[C:4]1[N:3]2[C@H:2]([O:11][C:7]([CH:8]=[CH2:9])=[CH:6]2)[CH2:1]1

Komponenten

7

Edukt 3

HCID 11776TriphenylphosphineHCID 5280980Clavulanic AcidHCID 131711458HCID 131711458, Verbindung

Produkt 1

HCID 22807221HCID 22807221, VerbindungAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Clavulanic acid (1.5 mmole) in dry tetrahydrofuran (5 ml) under a dry nitrogen atmosphere was treated with triphenylphosphine (1.5 mmole) and then, dropwise, diethylazoxicarboxylate (1.5 mmole) in dry tetrahydrofuran (2 ml). After addition was complete (2 minutes), the mixture was stirred for 30 minutes at room temperature and was then ice-cooled and diluted with a mixture of ether and n-pentane (1:2, 20 ml). The mixture was filtered and the filtrate was diluted with dry benzene (10 ml) and then concentrated to about 5 ml under reduced pressure to yield a solution of the title compound (1 mmole).

Aufarbeitung

  1. additionAfter addition
  2. custom(2 minutes)
  3. temperatureice-cooled
  4. filtrationThe mixture was filtered
  5. additionthe filtrate was diluted with dry benzene (10 ml)
  6. concentrationconcentrated to about 5 ml under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-34b7a54a358440d7a798a5985e355b41
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145430

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